Ada Palmer – Machiavelli is the most misunderstood thinker of all time

Ada Palmer is a science fiction author, composer and historian at the University of Chicago. Dwarkesh opens with Machiavelli's own framing: The Prince is dedicated to Lorenzo di Piero de' Medici and given to him in 1513, and in the final chapter Machiavelli tells him he is the only person who can bring Italy out of its current ruin. Why were things so bad, and what is the historical context?

Palmer gives a two-part answer, conceding that any granular history has many parts: the papacy is one, the city-state structure of Italy is the other.

Start with the city-states. There is a principle in politics that when a government has had long continuity, it has a great deal of legitimacy: people believe in its institutions, they are used to it, and even when they complain it is still the government. Break that — overthrow the ruler, dissolve the republic, install something new — and the replacement does not have the same staying power. So it is very common for one regime change to be followed by five more, rapid fire.

The French Republic shows the pattern: republic, restored monarchy, republic, monarchy. When a long-standing thing cracks, you get chaos. England's Wars of the Roses are similar: one stable dynasty for a long time, and the moment a king is overthrown there is overthrow after overthrow, because the thread of continuity was cut.

In Machiavelli's lifetime that thread is cut for most Italian cities, which from his perspective guarantees more and more overthrows. When he was born, six or seven city-states had recently had their governments uprooted; by the time he writes The Prince it is dozens — in fact the majority. Almost no government has staying power; almost every one is ripe for yet another replacement. That is half the answer to why he perceives such urgency, and such certainty that stability is impossible.

The other half is the papacy, a long and evolving organism — one of the oldest institutions in the world now, and one of the oldest even then, five hundred years ago. And when power is centralised in an authority, especially an executive, how that executive uses the power can change, with each holder setting norms for the next.

Over Machiavelli's lifetime and just before it, a run of consecutive popes expanded executive power, especially on the military side, launching more wars and arbitrarily overthrowing governments. A number of city-states are directly ruled by the papacy, and in theory the pope can appoint anyone to rule them. Here is a pope with an illegitimate son he wants installed somewhere, so he overthrows a city's government and puts the son in. The next pope does it to three cities; the next to five. Soon there is a precedent that every new pope feels entitled to knock over any pawn on the board.

Once that is the norm, even a fairly nice pope inherits the idea that the papacy overthrows and replaces governments. This creates an instability unique to Italy, because there is no predictability about who the next pope will be. It is not hereditary; you cannot plan for it. The next pope is elected — and very often elected by a coalition of everyone who hates the current pope.

Electoral politics tends to swing: those outside power work hard to get in with the next regime. Assume a papacy averages ten years in this period. Every ten years you get a completely unpredictable new monarch, almost guaranteed to be an enemy of the old one, who will therefore rip up everything that monarch tried to do.

So when Machiavelli writes the last chapter he is looking around at a perfect storm: practically every polity in the region has just had the thread of legitimacy cut, its institutions have no traditions, its people are not invested in its current rulers. These are pawns that have been knocked over before and barely stood up again, ready to fall. Meanwhile nothing will stop the turnover of popes. The only thing that could is one person gaining enough power and ascendancy near the region, with staying power and sons and heredity, to do what Cesare Borgia tried: have enough power near the papacy to strongly influence the next pope, and create a stability otherwise impossible.

Dwarkesh summarises: he wants the Medici not to unify Italy but at least to stabilise it.

Exactly — by having conquered enough of a chunk that the papacy fears them and must negotiate, rather than the papacy being surrounded by small weakened powers that will be turned over again and again.

Dwarkesh notes the pope at that moment is himself a Medici, which makes it even more plausible.

Before The Prince, Machiavelli is a bureaucratic diplomat who meets many of the famous figures of the age. Dwarkesh wants to know what he made of Louis of France, Maximilian and the Holy Roman Empire, and above all of Cesare Borgia.

Palmer says much of The Prince is spent trying to veil how much more he cares about Cesare Borgia than about anyone else. He tries to be balanced, moving through example after example, and sometimes he simply cannot.

There is a magical moment when he discusses Valentino's fall: the point where Borgia had amassed all that power and conquered almost everything in Italy, and then both he and his father the pope fell ill at once. Machiavelli writes that everything Cesare did, he did right — he conquered the kingdom and would have kept it; the only reason he lost it was fortune.

What he should say is that Valentino planned for every contingency at his father's death except the possibility that he would also be at death's door. That is not what he says. He says: he told me that he had planned. The first person breaks in. The historian can no longer veil himself; he cares too much.

It is a moment where the veil between author and reader tears. All the others Machiavelli observed from a distance, but he was in the room next to Valentino through all of it — the most incredible, life-changing, first-person view of a man so unique, charismatic and terrifying that accounts of him range from "the most charismatic leader I have ever met" to "this man was supernaturally charismatic, therefore he must be the Antichrist or an incarnation of the angel of death." Machiavelli was in the room, and every so often you feel that he is still under the spell of this figure at whose side he had the scariest job in the world.

The Borgia plan is clearly to conquer the Papal States in the middle of Italy. Tuscany, Florence's dominion, is a little notch on the side of them, like a puzzle piece. Anyone with a map says: you have to conquer that, you cannot have a kingdom without it. There is no way to stop it. So what do you do?

Machiavelli's advice to his polity is that this time they will not succeed in persuading the conqueror to pass them by, and cannot bribe him permanently into doing something else. But they can buy time. They can absolutely and abjectly swear to do anything he wants, give him their forces and their money, pay him and help him conquer the rest, and betray their allies. Florence had a 300-year alliance to defend Bologna; he said they had to break it. The whole world is broken right now, so break every promise and every hereditary alliance and be at this man's side.

The only survival mechanism is to win through loyalty, support, and Machiavelli being at his ear whispering forever that Florence is loyal. That buys the boon of Polyphemus, the terrifying promise of the conqueror: I like you, my guest, I will eat you last. That is the republic's only hope, and that is Machiavelli's job — to stand beside the scariest man in Europe since Frederick Barbarossa and whisper that the Florentine Republic will support him and give him anything he asks; just eat us last.

Dwarkesh asks whether this contradicts The Prince's advice never to rise with the help of great powers, since even in success you have empowered someone stronger than you, at whose mercy you now are.

Palmer says this is not Florence aiming to rise, nor expecting to gain anything. This is Florence knowing it will lose. Machiavelli is very open that if Alexander had lived another year, Valentino would have finished his conquests, taken Florence at last, and it would have been over. But popes are mortal. Buying time is sometimes the survival mechanism.

So Machiavelli has this firsthand experience of being with Valentino through all these decisions — including at the massacre at Senigallia, when rumour reached Valentino that some of his people were terrified of him and plotting to overthrow him. They were so frightened that they decided to abandon the plot, and he heard. He met them and said: I forgive you, it is fine, you have renewed your loyalty, you have passed the test, I trust you, all is well. He invited them to the banquet and massacred them all. The forgiveness was false; the betrayals were punished.

There is an amazing letter a couple of months afterwards, from Machiavelli's loved ones in Florence, after they finally receive a letter from him following the massacre. They say: thank God you are alive, we had no idea, all we heard was that he had massacred a large number of the people who were with him. It took months — the postal system had completely broken down in the chaos — for them to learn he was still alive. They did not know whether he had been caught up in the conspiracy; he could easily have been on a list of names the conspirators meant to recruit. So his wife, his children and his loved ones waited months to find out whether he too had been slaughtered. To them it felt like a miracle that he had not.

It meant he watched these deeds: you encounter them, you forgive them, you renew vows of amity — sacred vows taken in the cathedral — and then you slaughter them at dinner, violating the laws of hospitality. Dante would say that is such a grave sin that you are not merely damned; a devil comes up out of Hell, takes your soul out of your body and inhabits you. You are already in Hell while your body still lives. And yet it works: the rest of Valentino's men are more loyal afterwards than ever, and will not even whisper to each other about dissatisfaction, because the faintest whiff of conspiracy might mean death.

So why does Valentino's kingdom, for which he did everything right, fall apart? Because he happens to eat the same thing that gives him food poisoning as his father, and happens to be ill at the wrong moment. Also the puppet he gets elected, Pius III, dies too fast, and then he is outmanoeuvred by Julius. Had those things not gone wrong in a row, the kingdom would have stood — and he would have conquered Florence.

Machiavelli keeps reminding us that, yes, there are all these things we can try to do. We can remember it is better to be feared than loved. We can remember not to be hated. But we have power over, at maximum, half of what causes outcomes. The other half is always fortune. We know he is the origin of utilitarian thought, and that he says we must evaluate people's deeds by outcome — but he does not just say that. He says we must evaluate their deeds by what the most probable outcome was before fortune intervened.

So people look at Valentino Borgia and say: but the Borgias fell. They were feared, then hated, then they fell, and their enemies took power and chiselled their coats of arms off every surface in Rome — so that to this day you sit down at a pizzeria and there is a weird scar on the wall where the Borgia bull is no more. People want the moral to be: do not do what the Borgias did, they fell. Machiavelli says no — they did not fall because of their choices. They fell because half of what happens in the world is never in our control. You can do everything right and still lose. But we have to evaluate what would have happened, and therefore we should imitate them, because everything they did was right.

Dwarkesh's own prior misconception — from not having read these books — was that Machiavelli says the means do not matter, only the end. There may be a virtue-ethics sense in which he does not care about means, but he is far more concerned with means than one would naively expect. The means by which you achieve power determine how stable and how fruitful that power will be.

In military conflict he says that if you achieve power with the help of mercenaries, or with the help of great powers who end up stronger than you as a result of your victory, you are in a very precarious spot. But speaking of Julius, he makes a different point: if you achieve power by lying, by breaking oaths, by being unfaithful, that is fine — because people will forget that you are not faithful. They will take you at your word the next time they encounter you.

It is a genuinely interesting meditation on which means produce stable power and which do not. The fact that he thinks breaking your word is fine is not the whole story, though — it is subtler than that. If you are someone who breaks your word, and you break it in this way, it will bite you. If you break it in these other ways, it will be fine.

He analyses Savonarola, who made prophecies and promises, some of which came true and some of which did not, and who then made new ones and corrected what he had said the day before. In Machiavelli's analysis he handled his manipulation and his untruths badly, in a way that did turn people against him and cost him power. Partly because Savonarola, as a religious demagogue, had a power base whose core was people believing he was divinely inspired and would not err — so his base was fragile with respect to untruth. Given the specific shape of his power and the specific way he handled his contradictions, the lying did hurt him.

Whereas someone like Cesare Borgia makes an alliance, works with that ally for a while, then betrays them — and because meanwhile he was such an effective conqueror and so scary, even when he betrayed an ally, his other allies would say: I had better be more faithful to him, so that the next person betrayed is not me; I had better work hard to stay in the prince's good graces so I am not next. They did not turn on him, because he was so frightening.

Savonarola was not frightening. Savonarola was charismatic, persuasive, with one of those voices that made crowds thrill and women swoon. Decades after his death, when people asked Michelangelo what Savonarola had been like, his answer was: I still hear his voice. He had that kind of charismatic presence — and it was not enough once he started flip-flopping on policy and truth. Valentino was so scary that he could betray his top general, seize his lands and overthrow his city, and all his other generals would say: better step even further into line.

So it is not that lying is okay; it is that lying is sometimes okay if you check these other boxes, and not if you do not. This reinforces how far he zooms in on means. Do A and B and you are fine; do A and C and you are not. He looks at the minutiae of the different ways you can wield power and the different reasons people can have to follow you. If you are a prince who has invested in being loved, you have to keep it up, or cultivate being feared alongside it. If you have invested heavily in being feared, there are things you can do that a prince whose power rests on being loved cannot.

This reaches the famous line in The Prince: it is better to be feared than loved. What he is getting at, Dwarkesh suggests, is a deep cynicism about human nature. If people make you a promise, they will go back on it. If your power base depends on people's promises and loyalties, then as soon as your rule looks like it is tattering, they will renege. If instead your rule depends on people expecting that breaking their oath to you will be punished, that is far more stable.

He basically thinks people will behave as badly as they are allowed to — whether they are the tyrant, the people, or the nobles. This goes back to The Discourses. His whole justification for checks and balances is not unlike the American founders' reason for wanting checks and balances and for setting factions against one another: he is simply cynical, and thinks people will act as badly as you permit them to.